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<h1><a href="https://archiveofourown.org/works/29568399">The Almost Perfect Night</a> by <a class='authorlink' href='https://archiveofourown.org/users/BulletStead/pseuds/BulletStead'>BulletStead</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Chicago PD (TV)</td></tr>

<tr><td><b>Genre:</b></td><td>Abusive Relationships, Angst, Domestic Violence, Drama, F/M, Fluff and Angst, Gun Violence, Happy, Hurt Hailey Upton, Love, Pain, Protective Jay, Teasing</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2021-02-19</td></tr>

<tr><td><b>Updated:</b></td><td>2021-02-19</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-15 22:28:49</td></tr>

<tr><td><b>Rating:</b></td><td>General Audiences</td></tr>

<tr><td><b>Warnings:</b></td><td>Creator Chose Not To Use Archive Warnings</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,928</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/29568399</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/BulletStead/pseuds/BulletStead</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Jay Halstead had a plan to take Hailey Upton out for dinner, he had it all planned out in his head, but he didn’t expect things to happen so quickly as they escalated.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Jay Halstead &amp; Hailey Upton, Jay Halstead/Hailey Upton</td></tr>

<tr><td><b>Comments:</b></td><td>12</td></tr>

<tr><td><b>Kudos:</b></td><td>27</td></tr>

</table>

<a name="section0001"><h2>The Almost Perfect Night</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>This does have domestic violence in it with the people they meet, if that triggers you this fic might not be for you.</p>
    </blockquote></div><div class="userstuff module">
    
    <p>It had been a couple weeks now since Hailey and jay have been dating. Everything has been great, except a few forks in the road here and there, but they make it work because they’ll always be good together. Tonight was a special night, jay has it all planned out for them. </p><p>It was the night he would take her to bortoli’s. They had talked about this when she was in New York City and jay didn’t feel it was yet time to go there but tonight felt just right. There were no more cases involved, they finished work pretty early and they didn’t stumble on rough ones either.  He wanted to make Hailey feel special cause she is and he remembers that day on the phone with her how he promised it in his voice he would take them there. He wanted to spoil his woman.</p><p>“Jay... where are we going? You know you can tell me or I can use my detective skills on you.” She challenged, smirk crossing slowly over her lips. Jay just let out a soft laugh as his eyes made his way to her on the passenger side. “I’m not telling you, you can try to use your detective skills on me, but I want this to be a surprise if ya don’t mind.” </p><p>Hailey felt kinda pouty at this, she thought for sure she would get him on the last statement. He seemed determined on this ‘surprise’ she could try to pry it out of him more but she knew once Jay had his mind set that it would be hard to change it. “Alright, I’ll behave.. but just this once!” </p><p>Another laugh left his lips, tonight was going to be a good one or would it? Pulling into the parking lot he turns the truck off and gets out with her. He quickly walked to her side before she could get out. “Woah, I’m getting gentleman Jay tonight? How sweet. I wonder how long it’ll take before devious, naughty jay comes out.” She winked at him flirtatiously as she took his offered hand. </p><p>“We’ll see, that is if you can behave for tonight for me. Maybe, just maybe I’ll reward you for it.” He shut the passenger door once she was out and took her hand as they walked side by side. She stopped for a second and smiled so big as she saw the red awning and the bold letters on the front of it. “I remember this being a discussion back when I was in New York City... it was with a fine looking detective that was sadly in Chicago.” She teased as she side eyed her boyfriend. Jay loved her reaction, it’s what he wanted. He played along with her teasing. “Oh yeah? fine looking you say? Never heard of that guy. Maybe I should kick his ass for talking to my girl.” A stranger opens the door for them, as they make their way up to the front entrance, a thank you coming from both of them simultaneously. </p><p>“And waste his idea of taking me to this place? Not a chance Jay Halstead.”as Soon as they went in, they both could smell the strong hint of pizza sauce filling the room around them. The aroma made them even hungrier than they already were. Pizza didn’t sound so bad. It was like Jay just knew what she was craving too. </p><p>They find a spot together, the waitress coming over asking what they would like to drink. Jay and Hailey looked at each other knowing what the other wanted. They both order it at the same time. “Soda.” When she left Hailey is laughing softly. “Have you ever been here?” </p><p>Jay can’t really look at the menu. He’s looking at Hailey, how beautiful she looks. He could get lost in this moment but her question grabs his attention back to reality. “No, I’ve always heard of it, but never been here until now.” She smiled softly, she can’t imagine he’s been here all this time and he’s never been to bartolis. It seems unrealistic. </p><p>“Are you sure? How long have you been here?” Jay laughs and gets defensive in a playful manner. “What? You saying I live under a rock?” She tucks her lower lip into her mouth smirking at him. “Well, I’m not saying you don’t.” </p><p>Hailey had a playful tone in her voice, jay loves the dynamic between them. It’s easy to be with her. It doesn’t feel forced, it feels natural between them. He especially loves her playfulness. Who knew he would let anyone see this side to him again? </p><p>“Ha, ha, funny Hailey. I’ll have you know I’ve been to many restaurants while I’ve lived here.” She leans forward with a shine in her eyes that Jay has never seen before. “Prove it Mr know it all.” She challenged him quietly, ever so low between them as if it was a dirty secret she just told. </p><p>“Well... I’ve been... to the purple pig.” She gestures for him to keep going and all he can think after that is Molly’s. Wow, he does live under a rock? “Okay, you know what change of subject. What do you want?” She laughs out loud, she looked so giddy as she got him tongue tied. “No! Finish it. Go on I’ll wait. You can’t expect me to hear you say purple pig then stop.” </p><p>Jay is flustered now, he can’t cause then she’ll know she won. He shakes his head. “I think I’m good. How about that pizza?” He tries to change the subject again but Hailey is stubborn. “No, come on Jay.” </p><p>He grumbles with a roll of his eyes, the waitress coming back with their drinks. They point to what they want, their staring contest never broken. “Only that and Molly’s...” the waitress is gone and walking away. Hailey looking so smug in her seat. “I knew it. I won.” Jay shakes his head pointing a finger at her. “You can’t win, you didn’t tell me yours. It’s not a fair game if you don’t tell me where you’ve been to.” </p><p>They’re laughing and looking happy, they bicker back and forth on this subject. The pizza winning the game over since their stomachs were empty and the sight of it was mouthwatering. They smile together as they eat, they’re enjoying their conversation about where to go next on a date. </p><p>A married couple walk in taking a seat next to them. At first Hailey thought nothing of it. They seemed like good people but then she quickly saw the signs as the wife knocked a drink over and her hands shake as she cleans it up. Hailey smiled to the woman asking if she needed help. </p><p>The husband told her to mind her business. Jay snaps his head in his direction. He didn’t like the tone of the mans voice to his girlfriend. “She’s just trying to help. Why not help your wife if you won’t let her.” Hailey didn’t like where this was going. She swallowed her bite of pizza looking to Jay to drop it, but the husband snapped back harshly to the detective. </p><p>“What did you say? How about you mind your business on your side and leave my wife alone.” This wasn’t looking so good. His energy he gave off was bad and Hailey couldn’t stop the feeling in the pit of her stomach that he was bad news. “Tell her honey, you don’t need help. See she’s got it.” </p><p>The woman repeated his words and cleaned up the mess quickly as possible. “Yes, I am fine. I don’t need any help it’s okay.” She sounded like a robot if you asked Hailey. She dropped it though and as the woman got up to throw the trash away. Hailey did too getting up and meeting with the woman telling her it’s okay and here’s her card. </p><p>The husband gets up out of his seat, Jay right behind him. He didn’t like this guy. He couldn’t put his finger on it but he had a gut feeling he should keep his eyes on him. The other male demands for him and his wife to leave. They should find a new spot. </p><p>Jay wanted to say something but Hailey stopped him. He nodded his head. The married couple walking out now, Jay tells Hailey he’s gonna go pay the bill and they can leave. He knows she doesn’t want to stay much longer. He can feel how uncomfortable she is not just by looking at her but also knowing her for so long. </p><p>“Yeah, that sounds good. I’m going to go to the bathroom.” She kissed his cheek on her tip toes then they go separate ways. As Shes walking by the door towards the bathroom, she saw the husband trying to force the wife to get in the car. She seemed reluctant to get in. </p><p>Hailey decided she’s had enough, this needed to stop, she needs to do something. She marches out the door the screams a hey to the dysfunctional couple. The man growls for his wife to get in the car, she still was squirming to get away. “I think you should let go of her.” </p><p>This again? The man thought, doesn’t this couple have anything better to do then be in his marriage? “You again? Why don’t you get back inside and enjoy your damn pizza! Come on sweetie, get the damn car!” </p><p>The guy needs a reality check, that’s not how you speak to your wife and she sure as hell won’t put up with it. She gets his attention and signals the woman to run. She gets free from her husband, but he goes to grab her. Hailey gets in the way telling her to run. </p><p>The husband is too quick, he drags his wife back by her hair and pulls a gun out, pointing  it at Hailey. “I suggest you get back in now before something happens.” Hailey backs away slightly trying to diffuse the situation. "Look I know you don't want to hurt her. So put the gun down." Hailey wished she had her gun on her now. Why didn’t she bring it? Oh yeah cause she thought she’d have a nice dinner date with Jay, not a crazy man with a gun. </p><p>“I am sick of you treating me this way! Stop with the guns Harold! She’s just being nice!” It was the woman who spoke up. She was taken aback by this bravery. She’s proud she spoke up but this was a dangerous situation. </p><p>“Really Rebecca! She’s trying to take you away from me! Now get in the fucking car!” He still has his gun pointed at Hailey, as the husband is distracted Hailey goes to fight him to take the gun out.</p><p>Just as Jay finished paying, he went looking for Hailey. It doesn’t take long to go... he knocked on the door but no answer. He then heard gun fire, making him alert. He rushed outside. The husband speeding off and Hailey bleeding out as he ran to her. He bends down feeling tears in his eyes. </p><p>“Hailey! Stay awake Hailey! Don’t close your eyes. I’m here baby.” He’s crying so hard as she’s coughing up blood and laying on the ground. She’s trying to say his name but can’t as more blood comes up. She watched as Jay called for help and held her in his arms. That was the last she saw of Jay before her vision went dark.</p>
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